


Jessie Catches a Pokemom

by DraceDomino



Category: Pocket Monsters | Pokemon (Anime)
Genre: Deepthroating, Dirty Talk, F/F, Futanari, Humiliation, Mindbreak, Rape/Non-con Elements, Revenge, Rough Sex, Wet & Messy, ball worship, musk
Language: English
Status: Completed
Published: 2018-08-24
Updated: 2018-10-15
Packaged: 2019-07-02 02:44:50
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 2
Words: 9,449
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15787344
Author URL: https://archiveofourown.org/users/DraceDomino/pseuds/DraceDomino
Summary: Infuriated at Ash's many victories over Team Rocket, Jessie decides to strike where he doesn't expect - by turning his mom into a desperate, depraved cocksleeve! Delia doesn't put up much of a fight, guess she took the "surrender now" option laid out in the Team Rocket motto.





	1. Chapter 1

Jessie Catches a Pokemom  
-by Drace Domino

For almost five hours now, the same mouth that kissed Ash goodbye at the beginning of his Pokemon adventure had been wrapped around his greatest enemy’s cock. Delia Ketchum was one of the sweetest older women in Pallet Town; always kind to everybody and so very, very proud of her Pokemon trainer son. Every morning she’d be out front watering the plants and boasting about Ash’s latest victory; how he had won another gym badge or how he had stopped yet another nefarious plan of the wicked Team Rocket. She was her son’s biggest fan, and nothing could make her think otherwise. At least...up until five hours ago. At least until she went back into the house after watering the plants and getting the newspaper, only to find a woman sitting at her kitchen table with her feet up, her hands folded behind her head, and a dominant smile spread across her face.

“Who...who are you?!” Delia gasped in sudden shock, her eyes going wide at the sudden home invader. The woman sitting around like she owned the place was much younger than her; only a few years older than her son. She was slender and cocky in every motion, with long, sweeping red hair in one of the most gravity-defying shapes Delia had ever seen. A solid white uniform with a ludicrously short skirt complimented kneehigh leather boots, and the bright red “R” on the white midriff top told Delia enough to know the answer for herself. She even verbalized as much as she dropped the newspaper, and slowly began to back herself towards the door. “Y...You...You’re Team Rocket, aren’t you?”

“Oh, looks like the twerp’s mommy isn’t as stupid as he is!” The invading woman gave a laugh, raising a gloved hand up to her face as she tilted her head back and cackled. Her gloves matched the leather of her boots and went all the way up to the short sleeves of her top, leaving no part of her flesh visible across her arms. Granted, the exposed belly and the spot between her skirt and her boots made up for it - it was at the same time a revealing and strangely conservative outfit, the outfit a woman that wanted eyes locked to particular parts of her. As she looked back towards Delia with the same dominant smile spreading on her ruby red lips, the woman’s voice filled the air with a menacing, intense tone. “That’s good to know. I’m going to be giving you a lot of orders, and I don’t like repeating myself!”

Delia was smart enough to know trouble when she saw it, and she wasn’t about to stick around. With a sharp cry she spun on a heel and started to race towards the living room, hoping to reach the door and make her way to freedom. If Team Rocket was really in town, that spelled bad news for everyone! Pokemon through the entire town were in danger, or at least...so she thought. She didn’t make it much further than the doorway in the kitchen; however, for her new friend was swift with a Pokeball.

“Wobbuffet, go!” She cried out, whipping a ball forward as it opened and released her chosen creature. The big blue blob appeared right in the doorway as Delia tried to run by, and its naturally buoyant and durable body sent her suddenly spinning right down to the floor. Delia gave a wince as she was sent down, her ass striking the tile floor of her kitchen as the creature gave a big, joyful salute.

“Wooooooobbuffet!” Its enormous smile didn’t haunt Delia for long, since no sooner did it appear did its owner call it right back. A flash of red light pulled Wobbuffet back into his ball, and moving to stand in the doorway blocking Delia’s path was the woman herself. Her voice, sinister and sadistic, was just a taste of the cruelty that Delia had coming her way.

“Prepaaaaare for trouble!” She roared, lashing a hand forward and striking a dynamic pose. “To protect the world from devastation...to unite all people within our nation!” James wasn’t around, so she had to carry the full weight of their motto by herself. “To denounce the evils of truth and love, to extend our reach to the stars above! Jessie! Team Rocket blasts off at the speed of light, so start sucking my cock or prepare to fight!”

There was a pause in the room as Delia took in the words, and as her head started to tilt upwards Jessie followed them with a soft laugh and a slow tug of her skirt.

“...Meowth, that’s right.” She cooed, just as Delia’s eyes fell on what was waiting for her. Ash’s mother still sat prone on the kitchen floor, looking up from Jessie’s boots only to see an enormous cock hanging down between them; so big that it was easily visible under the hem of the girl’s skirt. It was stiff, twitching, and as Delia’s eyes fell on it the thing only seemed to bask in the attention. It started to angle upwards through no motion of Jessie’s own, eventually lifting up the hem of the skirt as it started to point towards Delia. Heavy balls hung underneath and even from that distance Delia could smell her; a noticeable musk that filled her senses with every gasping, terrified breath.

This was...not how she had expected to spend her Monday morning.

“What...what do you...wa-”

“Ugh! Don’t you listen at all?! The motto isn’t the same every time, you know!” Jessie responded in a downright bratty fashion, clenching one hand into a fist as she barked at the older woman. Her other hand pointed squarely at her throbbing cock, which swung back and forth and carried another burst of aroma to Delia’s nose. “You think I have this hanging out just for the fun of it?! You really are as stupid as your son, after all! Get...to...sucking!”

And with that, without any further introduction or pretense, Jessie grasped Delia by her ponytail and forced the older woman’s face right into her lap. She didn’t shove her cock down her throat just yet; hell, she was such a dimwitted thing that she wasn’t sure Delia would know what to do with it. For now, she simply forced the older woman’s face against the side of her cock, making absolutely sure that her nose was buried in the spot between her balls and the base of her shaft. A hiss of pleasure ran from the depths of Jessie’s throat as she rocked her hips from side to side, dragging her length across Delia’s features and making sure that she got plenty of long, deep breaths of her musk. She always had a particularly strong scent, and knowing that the twerp’s own sweet mother was breathing it in was enough to make Jessie shudder in pleasure.

“That’s it...get it all over your face, you miserable whore.” Jessie’s words were far more wicked and devious now that she got the motto out of the way, and as Delia gasped and struggled she only locked her hands tighter to the back of her head. One leg even lifted so she could brace her boot to the edge of the table; the better to grind her sweaty, scented nuts against the older woman’s face. Delia’s cheeks were red and her eyes watering from the shock of it all, and her hands were pathetically braced to Jessie’s thighs in an attempt to push away. An attempt that, naturally, was a complete waste of effort. Jessie merely laughed in dominant glee, gazing down at her newest and most delightful catch as she spoke. “Oh, I might not be able to beat the twerp’s Pikachu, but this is even better! I wonder what he’ll say when he finds out his mommy is a cocksucking whore?! How fun! Ohhh ho ho ho ho ho!” One of her hands lifted to brace just underneath her mouth as she tilted her head back, giving a joyful and cocky cackle.

Delia’s head was spinning from how fast everything was moving; not to mention the heavy scent of Jessie’s balls that was still steadily filling her lunges. It was a scent she couldn’t escape no matter how hard she struggled, and every last gulp and gasp of air was left laced with it rushing through her body and sitting inside of her. When she opened her mouth to give a scream there was quite simply too much of Jessie’s flesh to allow it, and all she managed was getting a taste of the Team Rocket girl’s nuts against her warm, wet tongue. As soon as her failed scream was left muted and muffled against Jessie’s lap the dominant woman cackled once more, looking down to where she could just barely see Delia’s face past the shape of her massive cock.

“Oh, you’re that eager that you want to start licking already, hmm?!” She beamed, tightened her hands against Delia’s ponytail once more, and gave her a tight jerk to keep her firmly in control. “Well, you won’t hear me complain! I can already tell you’re going to be a lot more willing to play than his little girlfriend was!” Misty had put up a fight, but Delia? Delia seemed all too eager to suck on Jessie’s cock - even if she wasn’t fully aware of that fact yet. Jessie shook the woman’s head from side to side by her ponytail; violently letting her balls batter back and forth across Delia’s face to further spread her heavy scent. Just after she finished she pushed the woman’s head down even further, and soon those sweaty nuts were resting against Delia’s forehead as her mouth was made to press right to Jessie’s taint. In that spot in between the girl’s ass and her sack Jessie’s musk was easily at its strongest, and the devious Pokemon thief pushed one hand to the back of Delia’s neck to make sure she was properly introduced. She forced Delia’s nose against it and held her there until she was sure she had to take in a few breaths, at which point she pulled at her ponytail until she could feel warm lips pressed to the sensitive spot of her taint.

And it was there that Jessie finally demanded action from her new bitch; her voice hard and stern, her eyes narrow, and her grip on the woman’s head absolute and unflinching.

“Start kissing, whore.” She hissed in a dangerous tone. After all, she had plenty of other Pokemon with her to make sure Delia did everything she was told...if her hand was forced. “Pretend you’re kissing the twerp as he jogs off to school!”

Delia, by that point completely overwhelmed and without any recourse or escape, did as she was told. Surprisingly easily, in fact. The older woman had been left alone while Ash went on his Pokemon adventure and despite her best efforts, she hadn’t been able to find a man to come home and please her since Ash’s father left. Jessie’s massive cock was the first one she had seen since those days, the first one she smelled, the first one she tasted. And now, with her lips parting and her tongue slowly slithering out to touch Jessie’s taint, she was already starting to realize it was the first one that a part of her...lusted for.

It was enough to make her eyes water from the emotion of it all; tears of joy, tears of fear, or simply tears brought by the heavy scent she was utterly incapable of escaping. Either way, as they rolled down her cheeks her tongue finally positioned itself at Jessie’s taint and started to lick, swirling slowly in a circle to that sensitive spot of flesh. A little further down and she’d be licking Jessie’s ass; any further up and it’d be the base of her balls. But in that one particular spot she had the best of both worlds, and the flavor was at its most dense and saturated, just like the scent itself.

“Ohh, that’s a good little slut!” Jessie cackled, only barely able to see Delia’s crying face from past her cock. She needed to push her balls to the side in order to make room, and doing so made sure that they glided past Delia’s eyes and smeared the tears over her face. A few threads of dishevelled hair stuck to Delia’s forehead and by then her ponytail had all but come undone, and she looked far from the sweet, inviting mom that everyone in Pallet Town knew her to be. She wasn’t about to go tend to her garden anytime soon; not when there was cock to suck in the kitchen!

“Listen up, slut~” Jessie let the words drip from her lips in a fashion that would’ve sounded sweet, were she not actively in the process of choking Delia with her taint. She even combed a few gloved fingers through the back of her hair, doing her best to straighten that messy ponytail that had come undone in the ferocity of the moment. While Delia’s tongue kept slathering back and forth across her taint Jessie spoke loudly and firmly with her orders, making sure that the older woman knew they weren’t to be refused. After all, she had plenty of instances to make up for in which her unruly sun attacked Jessie without any trace of provocation! It would take quite a bit of work on her knees to make up for it all. “You’re going to suck every inch of me down your throat. And it’s going to hurt. And you’re going to choke, and you’re going to cry. But when I cum, can you guess what you’re going to do with it all…?”

In that rare moment she pulled Delia’s ponytail just enough to get the woman’s mouth away from her taint, just enough to give her a chance to respond. And Delia, in that brief moment and that tiny opportunity to call for help, wasted in so she could answer the woman that had broken into her house.

“S...Swallow it…?” She whimpered, tears still marking the sides of her blushing cheeks and her voice aching from the weight of her words. Jessie merely beamed, and wrapped her fingers so tight through Delia’s hair that it made her entire scalp ache.

“Oh, you’re so much better behaved than the twerp’s girlfriend.” Jessie cooed as she wrenched her hands up, forcing Delia to her feet so she could drag her closer to the kitchen table. When they stood beside it the Team Rocket girl swiped a hand across the surface; dismissing the pitcher of orange juice and Delia’s breakfast right off the table to clatter on the floor below. And then, drawing in Delia’s face close to her own, Jessie let her breath strike the woman’s cheek as she whispered in slow, predatory fashion. “...I might just have to knock you up once I teach you how to suck dick.”

Delia didn’t have a chance to respond to what she could only perceive as a threat; for no sooner did Jessie speak those menacing words was she forcing Delia down to the table. The older woman gasped and cried out as she was forced to lay flat; her head dangling off the edge and her tangled hair nearly dusting the floor. Her slender, mature but still-fuckable body was splayed out atop the table for Jessie to admire, and she naturally yanked the woman’s shirt and bra right up and over her breasts to get a nice, long look at Delia’s body. Surprisingly full and firm breasts - it was a shame nobody had wanted to fuck her until now!

“These tits shouldn’t be covered up!” Jessie laughed, her gloved hands moving down to grope and grasp at them, just as her enormous cock lightly slapped Delia’s face back and forth. She could feel the older woman’s gasps and whimpers against her length and they only served to excite her further; every time Delia sobbed to the side of that pulsing cock she only made her impending throatfucking rougher. For the moment; though, Jessie seemed content to make Delia squirm by pinching her nipples to the point of bruising ache, and giving her full, motherly tits some rough slaps so she could watch them bounce. “Did little Ashy washy suck on these when he was a baby? I bet you never thought he’d grow up to get you into this kind of trouble! You should make sure to thank him when you next see him!”

A slow, cruel smile spread across her lips.

“In fact...let’s hear you practice.” She hissed, just as the tip of her cock dangled before Delia’s lips. “Say ‘Thank you, Ash, you fucked up so bad that I’m a worthless cocksleeve now!’”

“W...Wha...I can--mmmph!” Delia’s refusal to immediately say what Jessie demanded came at a price; a price that was extracted with the warm, wet grip of her throat. Jessie had shoved her cock forward without any hint of hesitation or pause, and her impressive inches pushed all the way down until her balls slapped to Delia’s wide eyes. She shrieked, she sputtered, her hands flailed and tried their best to fight against Jessie, but the Team Rocket girl was far too strong. Her hands locked around Delia’s wrists and she slammed them down to the table so hard that it made the woman flinch, and with the sculpt of her prick making Delia’s throat noticably bulge, Jessie spoke up again in an even harsher tone.

“If you won’t say what I tell you to say, you don’t get to speak at all!” Jessie ordered, gazing down at her handiwork and relishing in it. She could hear Delia spitting around her shaft and choking violently against it; the slut had no idea how to deepthroat a cock, and she likely couldn’t breathe with it all stuffed down her throat. Jessie didn’t particularly care - a lesson had to be taught. “So I’ll give you another chance, whore! Say what I tell you...or I’ll just keep throatfucking you so I get some use of your mouth!”

Even after throwing out her ultimatum, Jessie let her cock inside of Delia’s mouth while the older woman thought about it. A few more seconds of gagging and open sobbing, a few more seconds of failed attempts to claw at her gloved hands to release Delia’s wrists. A few more seconds of intense, glorious pleasure for Jessie by violently deepthroating her greatest enemy. For all she cared Delia could keep refusing - it only gave her an excuse to keep her mature mouth stuffed with as much cock as possible. When she finally started to pull back; however, she was pleased to find that Delia had decided to play along.

Jessie’s cock pulled out of Delia’s throat like a sword from a scabbard, and when it popped out of the woman’s mouth heavy coils of spit were dangling from the tip, which she naturally smeared across her face. And Delia, who was still fighting coughing and gagging and openly sobbing, knew that if she didn’t do as Jessie had said that she’d only receive more of the same. What choice did she have? It was...time to practice for when she saw Ash. For what she would say to her beautiful young son that she was so proud of when she next saw him.

“A...Ash...honey...t-thank...you…mmmphhhh!” She didn’t know why she was being punished this time, but she was. Jessie thrust forward to swab the mother’s throat with her cock for a few long seconds, pulling back and grasping her dick by the base so she could swing it back and forth, pummeling Delia’s cheeks with it. With no other instruction to go on Delia continued to say what she was told, even as she flinched and winced from the painful cockslaps hitting her face. “You...you fucked up...so bad...I’m...I’m a…”

“What are you, whore?!” Jessie roared in delight, and throated Delia once more time. This time while her cock was bulging against her throat Jessie released the woman’s wrist just long enough to reach out, slapping her own dick through the fabric of Delia’s throat a few times. The sobbing and sputtering that echoed from underneath her balls was immense, and only made the devious villain laugh all the louder. “Tell me what you are! Tell the twerp what you are! As loud as this fucked and battered throat of yours can manage!” When she pulled her prick out of Delia’s mouth once more the woman instantly responded, showing Jessie that she could behave. That she could be a good girl. That she could be an eager to obey-

“-worthless cocksleeve! Ash, I’m a worthless cocksleeve!” She cried out, her body spasming from the emotion in the moment and a building arousal within her that she couldn’t yet place. Had it really been so long since she had a cock inside of her that she was cherishing this abuse?! Was it just the heavy scent of Jessie’s musk muddling her senses?! She had no idea, but it actively terrified her just how easily the words poured from her weary throat as Jessie’s nuts continued to slap her face. “Mommy is a worthless cocksleeve because of yo-u-u-u-uuuuu!” Her voice devolved into sobbing, which Jessie naturally had no sympathy for. Instead, she merely positioned the tip of her prick once more to Delia’s spit soaked lips, quirked a brow, and responded in confident, calm fashion.

“Good.” She offered the woman that tiny bit of praise. “Don’t worry - you’ll get to tell him to his face soon enough.”

And with that, she began to truly facefuck her prize. There was no more speaking allowed from Delia for now; no more chance to prove her loyalty to Team Rocket cock by talking about what a whore she had become. Now, Jessie only wanted to use her prize to the full potential, and finally cash in on all the times that Ash had beaten her. She released Delia’s wrists knowing full well that she wouldn’t be putting up a fight anymore, and instead let her gloved hands latch against those lovely motherly tits of hers. Using them as handles, Jessie braced herself, spread her thighs, and began to rapidly, intensely fuck.

Delia’s head still dangled upside-down from the edge of the table, and her eyes were forced to close as Jessie’s nuts slapped again and again against her, battering her in a sweaty musk that she was becoming increasingly intoxicated by. The rapid thrusts that Jessie was throwing into her went just as deep as the training she had already been through, but since they were fast and fierce it was easier for the woman to pace to her breathing. She could just barely get in gasps of air between thrusts, and she could even work in a few sobs when Jessie pulled her dick out to give her a few more deserving cockslaps.

Otherwise, Ash’s mother laid flat on the table, her body limp and exhausted. Her legs dangled from the knee down the other side of the table, and underneath her panties and skirt she was soaked in a way she had never been before. Not since she was a young girl that went on a Tauros ride at the Pallet Town rodeo was she so confused about why she was wet - why her pussy was soaked to the point that her thighs were damp and she was leaving a puddle on the table. Jessie hadn’t even touched her pussy yet; hadn’t even laid eyes on it! And yet, Delia was feeling a burn of arousal sweep through her body that she could neither understand or restrain. All she could do was try to keep breathing in between moments of cock flooding her face, and listen to the words of the woman looming over her.

“That’s it! That’s it, you miserable old bitch!” Jessie hissed, her body shuddering in pleasure. She was near now, so very near, and she knew it would be the first climax of many. After all, she didn’t drop in and force herself on Ash’s mother just to cum once! They had a whole day ahead of them! “Get ready, slut! Get ready to drink every last fucking drop of it!” It gave Jessie tremendous satisfaction to see her enemy’s mother convulsing while she was throated, to hear Delia’s gags and sputters as her cock rutted the very depths of her face. And when Jessie’s moment finally arrived she shoved herself forward with every ounce of strength she could manage, her eyes rolling back in her head and her cock unloading a ludicrously heavy payload of cum straight down Delia’s inviting throat. “Here’s your reward, cunt!”

Delia, in all her years, had never gone anything quite so difficult. It felt like fire rushing through her as Jessie’s cum erupted down her throat, painting the walls of her gullet and rushing down into her belly. She knew from the very beginning it was simply too much for her or any woman to handle; her cheeks instantly puffed out from the weight of all that cream and though she struggled to pull her mouth away Jessie quite simply wouldn’t allow it. Ash’s mother’s eyes went even wider and her body thrashed around atop the kitchen table, a brief part of her wondering if she was about to be drowned in cum all thanks to her son’s horrible behavior! It burst from her nose and splattered against the underside of Jessie’s nuts, smeared all over her face, oozed out the sides of her lips, and completely saturated her throat. She tried to swallow what she could, but even the act of swallowing was outright impossible with how far down Jessie’s cock was shoved.

She could do nothing but let herself be filled, try to gulp down breaths of seed-scented air, and whimper and sob as her mouth was used as nothing more than a place for Jessie to dump her cum. And as she laid there choking and struggling with Jessie’s cream flooding her sinuses and filling her belly, she knew one thing for a fact: this was all Ash’s fault! She wasn’t particularly proud of her Pokemon trainer son in that moment; not when he was out catching Pokemon and having fun while he abandoned his mother at home to be throated and facefucked by one of his enemies. What a heartless little brat he was!

Jessie kept her dick stuffed into Delia’s face for some time, and only slowly started to pull back when it was time to let the older woman breathe again. As soon as her tip flopped from Delia’s lips she started to gasp and groan, swallowing what cum she could while desperately clinging for breath. Her face was a complete mess, but Jessie couldn’t even see it - she had simply moved forward, flopped her balls atop Delia’s face, and let the woman gasp for air right up against her taint once more.

“You did well enough to start, I suppose.” Jessie chuckled a bit, arching a brow and looking up and down Delia’s figure. The bitch’s tits were welted red from Jessie’s grasp, and her hips were still rocking back and forth from an arousal that she couldn’t control. It was enough to make the Team Rocket girl smile all the wider, and she briefly nibbled her lower lip as she planned her next step. “...now, time to go to the bedroom, slut!”

Once again, a cruel smile twisted upon her face.

“Specifically...the twerp’s bedroom.”

***

And there Delia had been for five long hours, forced into her young son’s small bed as she was made to worship Jessie’s massive cock and heavy, sweaty balls. The Pokemom had been stripped down to nothing but Jessie had worn her Team Rocket uniform the entire time, and she still hadn’t paid the slightest bit of attention to Delia’s pussy other than to slap it in a fierce reprimand. By that point Ash’s sheets were soaked with spit and cum and the glistening nectar of his mother’s juicy pussy, and Jessie was triumphantly sitting at the head of it, her musky nuts and bare ass resting on his pillow.

And feverishly working up and down that throbbing cock was Delia, cradling it in her hands as she willingly moved her mouth up and down on that massive member. She was starting to get good - able to take it down nearly to the hilt of her own volition, but at that point it was quite likely that her throat had gone numb from all the fucking it had received that day. Her belly was filled with layers upon layers of cum; so much so that she wouldn’t need dinner that evening, and Jessie hadn’t given her any sign that she’d stop feeding her anytime soon.

The wicked Team Rocket girl simply leaned back atop Ash’s pillow, threaded her gloved fingers through Delia’s hair, and kept the woman’s mouth dutifully servicing her throbbing cock.

Ash Ketchum might have humiliated her in the past, but when he saw what she did to his mother…?

Well, it’d make what she did to his little friend Misty look like mere training. The little brat was going to regret ever crossing Team Rocket!

End of Chapter One.


	2. Chapter 2

**Summary for the Chapter:**

> Ash comes home for a visit, unaware that Jessie has turned his mom into a whore addicted to futa cock. Surely he won't find out because Jessie will absolutely behave in a fashion that's discrete and appropriate! Right?

Jessie Catches a Pokemom  
Chapter 2  
-by Drace Domino

Usually, Delia couldn’t be happier when Ash came back home for a visit. It was always nice to see her son again and catch up on all the adventures he had enjoyed during his Pokemon journey. She learned about the new friends he made along the way, all the new Pokemon he encountered, and never got tired of listening to him boast about all the badges he collected or the great victories he achieved. She was endlessly proud of her son for everything he had done, and it wasn’t uncommon for tears of pride to form in the corners of her eyes by the time she sent him off to bed safe and sound.

That evening; though, after a visit just like any other, Delia had to lie about her tears. They weren’t because of how proud she was of Ash like she had told him - they were because she knew the second he was in bed the woman that had been controlling her for the past two weeks would be back. Once Ash’s little head was down on his pillow, Delia’s would be down on Jessie’s lap. Sure enough, a mere twenty minutes after Delia kissed Ash goodnight, she was on her knees right in front of his bedroom door and Jessie’s enormous cock was shoved down her throat.

“Ho ho...so the little twerp is resting nice and cozy, hmm?” Jessie beamed, a wicked grin spread across her features and her hands fiercely gripping Delia’s ponytail. The older woman was gagging and sputtering and gasping for air, but over the past two weeks she had learned how to handle these intense deepthroated moments. She had even learned to become aroused by them; shameful as it was. As threads of spit rolled from the corners of her mouth and splashed to the floor below, Delia braced her hands against Jessie’s hips and looked up at the other woman with a pathetic gaze in her eyes. She was more helpless than ever now, knowing that Ash was sleeping so close by and that she was at risk of him finding out what a whore she had become. Jessie; on the other hand, only seemed all the harder in the face of Delia’s peril. “What do you think, slut? Should we go inside and show him what a filthy cunt his mommy is? Wouldn’t that be a fun conversation for you to have?!”

Delia gasped and whimpered and tried to shake her head, but Jessie’s pistoning prick was too far down her throat to make it possible. By the time Jessie let her up for air the Team Rocket girl had already pulled open the door to Ash’s bedroom, and a wide smile spread across her face at the peaceful sight within. She grasped Delia’s ponytail and turned the slutty MILF to face her son’s bedroom as well, and Jessie’s voice lowered to a whisper so she didn’t disturb the gentle peace.

“Aww, isn’t that cute? I guess you weren’t always a worthless fuckhole of a mother - you did some things right, I suppose.” Jessie beamed, and with that, began to walk inside while dragging Delia behind her on hands and knees. Ash was sleeping contently, laying on his back splayed out as wide as he could manage, and at the foot of his bed Pikachu was sleeping just as peacefully in a position that mirrored his trainer’s. They’d be allowed to continue their happy rest so long as Delia did everything she was told - Jessie had no intention of waking the boy up...but if she did, he’d certainly have a hell of a sight to see.

Delia; wearing nothing more but a pair of soaked panties that she had been stripped down to a few moments ago, tried her best to wipe the tears and spit from her cheeks as she realized the depths of Jessie’s depravity. She was being fully exposed and shown off just mere feet from her sleeping son, and Jessie kept walking across the room on those thigh-high leather boots, moving ahead like a vicious predator. The Team Rocket girl’s cock was hanging out from underneath her miniskirt and still dripped of Delia’s spit - something that the woman would be thankful for in just a moment. When Jessie finally moved to the side of the bed she even gave a tiny smile to the sleeping Ash, and let her fingers tease across his hair before looking back to her kneeling slut.

“Come give him another kiss goodnight, whore.” She demanded in a hushed whisper, and wrenched her fist within Delia’s hair to encourage the woman’s obedience. With a gasp and a groan Delia was forced to her feet; stumbling ahead and only barely catching herself with her palms pressing to the headboard. Her heart was racing beyond measure and fear traced her weeping features, and when she looked over her shoulder to glance at her abusive owner Jessie merely gave her a stern glare to show she meant business. Delia had two options in that moment - do what Jessie demanded and risk Ash finding out about her past two weeks of sexual service to his greatest enemy, or refuse the woman’s demand and make that knowledge a certainty. With a quivering hope that Ash was just as deep a sleeper as he was when she would wake him up for school, Delia leaned in, her lips tight and her eyes closed as she did as she was told.

A soft kiss on her son’s cheek, like any good mother...although most good mother’s didn’t have lips that were completely coated in cock-flavored spit. But when her lips touched Ash’s cheek she very nearly broke her own cover with a sharp cry - for it was in that moment that Jessie had decided to take Delia’s ass. The older woman’s eyes went wide and she bit down on her tongue to stop herself from screaming, and when she cast a look over her shoulder once more Jessie was already holding her hips and pulling her panties aside - just enough to make way for her enormous cock. On trembling knees Delia was forced to brace herself, and as she swung back and forth with every one of Jessie’s thrusts the spit clinging to her lips and cheeks dropped down to Ash’s face. Just one of many, many shameful moments yet to come for the mature beauty of Pallet Town.

“I’m a sucker for sweet moments like this.” Jessie purred in a soft voice, just as she hilted her cock within Delia’s ass once more. “Again, cunt. He must miss his mommy!”

Ash was a young man by now, but that much was certainly true. He had rambled on just a few hours ago about all his wonderful journeys just like when he was little, his enthusiasm seemingly being the one thing that never changed. And Delia, still with the mental image of the boy that had grown up so fast during his adventure, had to turn back and give him another kiss goodnight. And another. Each feather-soft and spreading her cocksucker spit, each always at a risk of being pushed too far ahead by one of Jessie’s thrusts, or simply erupting into a sharp cry as the dominant villain fucked her. She kissed Ash from cheek to cheek and even across his resting lips, and still he didn’t wake. Sure; he stirred, murmured, even licked his lips within his sleep - but not even the flavor of his mother’s dick-tasting spit was enough to wake him up.

Jessie, beaming from ear to ear, locked her hand against Delia’s ponytail and suddenly yanked the woman’s face back to her. For a few blissful seconds she was away from Ash’s face and no longer afraid of accidentally waking him, but her relief melted into shame and humiliation as Jessie slapped a gloved hand across one of Delia’s tits, squeezing it fiercely while the other hand wrenched at her hair. She leaned in close, drug her tongue across Delia’s throat in lusty fashion, and continued to whisper even as the sound of flesh slapping on flesh filled the room between them.

“You’re such a filthy whore…” She whispered, and forced Delia to look down at the mess she had made of Ash’s face - not to mention the two shadows cast atop his body that were still in motion. As Jessie thrust her cock to the depths of Delia’s ass and made it almost impossible for the older woman to prevent from crying out, her voice continued slithering out in a wicked tone for the delighted pleasure of continuing to dominant her. Her body, her heart, her soul. After just two weeks, Jessie had trained her pet bitch better than any Pokemon...and fucking her ass raw a mere foot away from her son was proof of that. “I can tell how much you love this, you miserable cunt. I remember how you were begging me to fuck you last night. You said you’d do anything if I came in your ass...surely you remember?”

Delia remembered. She remembered in horrible, lucid detail. After her past two weeks of abuse she had become a wonderfully broken sex slave for the Team Rocket woman; willingly throwing herself down to her knees to worship a cock that had given her pleasure unlike anything she had ever known. Even now, with fear and panic rushing through her, with the taste of her son’s lips on her own, she was still wet beyond all reason. Her ass, unable to feel the same shame as its owner, was gripping and trying to milk Jessie’s cock just like it had done the night before. The mother of one of the world’s greatest Pokemon trainers was nothing more than a cocksleeve for a Team Rocket grunt - and she absolutely relished in. Even if her heart was breaking more and more as she watched Ash’s peaceful, sleeping features.

“I...I remember...I…” Delia swallowed and bit down on her bottom lip, trembling and letting her hands lower. She hooked her thumbs against the waistband of her panties and did the work of starting to pull them down - something she was only able to do until they hitched against the side of Jessie’s cock. As they dangled there she breathed out slowly and with an intense heat rising within her; hoping in that moment that she could have it all - a peaceful life as a mother to Ash, and a lusty night life as Jessie’s depraved whore. “...please...take me to...to my bedroom?”

She’d do anything Jessie wanted in the bedroom. The redhead could have anything she desired; any hole, any position, no matter how much it hurt her or scared her. Her body would be Jessie’s fucktoy if only they could go to a private bedroom to do it; someplace where they weren’t at risk of Ash sitting up and seeing what a disgrace his mother was.

Unfortunately for Delia, Jessie knew something very important.

She knew she could have all that no matter where she chose to fuck her toy.

“You know, watching you kiss the twerp goodnight got me to thinking…” Jessie mused; outright ignoring Delia’s request. She popped her cock out of the woman’s ass so Delia could finish dropping her panties, and nudged her forward even closer to the bed. Her voice was low so as to not awaken the runt, and when she spoke she scooped one of her hands underneath Delia’s knee, lifting her leg up slowly until she could press her foot towards the headboard. Another hand moved Delia’s opposite knee to the mattress itself, and as Delia was left frozen with panic and horror and arousal she couldn’t explain, her pussy was left hovering mere inches above Ash’s sleeping, peaceful face. Jessie didn’t speak again until she had Delia into position, but once she had the older woman keeping her cunt one gasp away from her son’s lips, the devious redhead finally had the chance to announce her plan. “...I think I’d like to have a little brat of my own. Good thing I’ve got a bitch that doesn’t mind getting knocked up.”

Her words came just as the tip of her glistening cockhead pressed against Delia’s pussy - sending thrashing, wild emotions through every inch of the older woman. Jessie’s words were outright madness, announcing a full desire to breed her captive MILF, and yet Delia’s soaked nethers were nonetheless inviting to that throbbing cock as it slid inside and spread her folds. Delia’s heart was racing so rapidly she was quite sure she might faint, and she only managed to keep herself up and balanced by the knowledge that if she dropped Ash would suddenly feel his mother’s pussy slam against his face. With a tiny whimper that she desperately hoped wasn’t enough to wake him, Delia looked back to Jessie with a look filled with sorrow, fear, panic, but most of all - a confused excitement.

Even if she hated herself for it, she couldn’t remember a time that she had been so excited or felt so alive...or that her pussy so desperately needed to be filled with cock.

Jessie didn’t hesitate to give Delia exactly what the filthiest part of her was craving, and she jammed her cock inside the older woman’s soaked slit right down to the hilt. Delia was forced to bite down hard on her bottom lip to prevent from crying out, and her palms pressed flat to the wall as she braced herself for what was to come. Jessie had taken to fucking her rough and brutally over the past two weeks, and though Delia’s mature figure had gotten used to being treated like a durable cocksleeve, she could only imagine how difficult it would be to maintain her senses as her pussy was plowed inches above Ash’s face. Every time the young man gave a tiny murmur or a little noise within his sleep Delia could feel new goosebumps race across her face, and tears of shame escape down her cheeks in wilder, hotter streaks. She didn’t hate Jessie nearly as much as she hated herself in that moment, and yet she did nothing to prevent the cocky redhead from using her so willingly.

“Ohh, you’re going to be such a good mother…” Jessie cooed, one hand moving around Delia’s bare belly and brushing up and down, fondling her and making her writhe underneath her grip. She pressed herself against Delia so that the woman felt Jessie’s tits against her back; brushing over her through the fabric of her Team Rocket uniform. With her mouth against Delia’s ear and her breath hot and heavy she whispered in a tone that became hungrier as the seconds passed, intensifying with every short, sharp thrust of her hips that forced her massive dick within those stretched walls. “I can’t wait to watch your pregnant bitch belly bounce while you ride my dick! Everyone in town will know you’re just a dumb pregnant whore that couldn’t help herself from getting knocked up by the first dick willing to shove inside her!” A sharp laugh came to her; so loud that it very nearly woke Ash. She pushed forward down to the hilt and savored the warm grip of Delia’s cunt; from the soaked delight to the way her muscles tightened and constricted against her shaft. Jessie’s voice was as harsh as ever, low and dangerous and cruel to an obscene degree. The only thing she loved more than fucking Delia was watching her new pet MILF squirm in shame and obedience. “...when your new brat asks about their Daddy, you can tell them all about how Mommy is nothing but a cocksucking, cumguzzling, worthless fuckslut!”

Delia, weak and weary and trembling so hard that her muscles were starting to give, could say nothing to dismiss Jessie’s claims. If the redhead wanted to knock her up, then that’s exactly what was going to happen - there was nothing she could do to stop it. The only question remained was what she’d tell the other people in town...and what she’d tell Ash when he asked about his new baby brother or sister. With her eyes wet and her nose running from the intense torrent of emotions running through her, Delia could only give Jessie a tiny, weary nod. A nod of compliance and submission, a nod that told the villain that she understood her new role in life. Jessie, in her infinite cruelty, couldn’t help but to twist the knife even deeper as she gave Delia one more sharp whisper.

“...maybe this time, the cock that puts a baby in your bitch belly will stick around.” She teased, and lewdly licked across Delia’s throat to make her squirm all the further. “But only if you behave.”

The words stung Delia deep, but she couldn’t deny that there was an appeal to Jessie’s promise. If she did well, if she behaved, if she kept making that massive cock happy...it would stay so it could keep fucking her. Keep making her cum. If that was truly on the line, then in that moment Delia found herself with no other impulse but to keep it. She looked back over her shoulder one final time to Jessie and though shame and humiliation were still worn on her face and down her cheeks in the form of warm tears, she gave the abusive redhead a tiny nod of agreement. Or at least...acceptance. If it meant keeping a cock around to please her, she’d do anything it asked. She couldn’t be alone - not again.

“W...Wha...Whatever you...want…” She whispered, just before her body went into an intense shockwave of pleasure. She spasmed violently in a sudden climax, and Jessie took advantage of the moment by giving Delia a thrust all the way to the hilt; pressing her hips forward until they slapped to Delia’s ass and she gave the women a few ounces of pressure. It was enough - just barely - to move Delia’s lap down to where her pussy grazed Ash’s face. The tiny tuft of soaked hair, the moist pink of her folds...both dancing across Ash’s sleeping features and leaving his nose a bit more moist for the exchange. The young man gave a drowsy murmur and absently rubbed his face in his sleep, and when Jessie realized just what happened she couldn’t help but grin as wide as ever. She leaned in against Delia once more, and as the older woman was still trembling in climax allowed her smooth cruelty to caress her once more.

“I haven’t decided yet if I’m going to fuck the twerp, too - or just let him watch what a whore I’ve turned you into.” She cooed, and rolled her hips from side to side to grind her cock against Delia’s walls. “I trust you’ll be happy with whatever I decide!”

And from there, Jessie began to fuck the older woman with such force and presence that Delia couldn’t find the strength to respond. She had to bite down on her forearm to prevent from shrieking as a second climax instantly crashed into her; the result of being so thoroughly dominated and owned beyond all reason. Jessie was pounding herself forward faster and faster as the seconds passed and it was a true miracle that Ash didn’t wake to see what was going on mere inches above his face; perhaps the glistening touch of his mother’s cunt across his nose and lips was enough to lull him into an even deeper sleep. No matter what, he didn’t stir the entire time Delia’s cunt was filled with cock no matter how wet and juicy she became, continuing to doze peacefully as nectar from above struck his cheeks, landed in his hair, or peppered his lips which he licked in his sleep from time to time.

Jessie shuddered in absolute pleasure; this was exactly what she had hoped for when she dropped by the runt’s house two weeks ago. The slutty, curvy MILF wrapped around her cock in perfect obedience, and Ash oblivious to just what was about to happen. The little brat had caused her a tremendous amount of frustration and pain over the years, but this...this made it all worth it. Jessie flared with passion as she tightened her hand on Delia’s ponytail and wrenched it painfully hard, just as her other hand squeezed one of the woman’s full tits to the point that she left red imprints from her grip. She was rough now; uncaring of whether or not she woke Ash up, her hips slamming forward harder and harder and harder as Delia’s figure melted around her. The whimpering gasps of the older woman were enough to drive Jessie berserk, and the tender, tight, moist grip of her cunt was fueling every wicked intention within her. As much as Delia was a servant to the dominant redhead Jessie too had little control; she could only do what her passions were telling her in that moment, and then and there her desire extended only so far as to fuck the curvy MILF and fill her up with rich, potent cum.

She was going to breed this bitch - and she was going to make her work her slutty ass off if she didn’t want to get knocked up and ditched for a second time in her life.

When Jessie’s climax finally came it was well within the span of Delia’s third or fourth; the spasming brunette seemed to have trouble keeping herself in check as she balanced her pussy above Ash’s face. As pleasure rolled through the Team Rocket grunt Jessie very nearly cried out, but managed to keep her tongue to the roof of her mouth as her impressive cock spasmed, twitched, and unloaded a torrent of cum that impressed even her. She could tell it was more than her usual payload, encouraged not only by Delia’s outright submission but by the fact that the twerp was sleeping oblivious underneath them - it was quite easily the most aroused Jessie had ever been, and the most intense orgasm of her life. When she had set out to ruin Ash’s life by fucking and breeding the women closest to him, she had no idea it would feel so...rewarding!

Her cum pulsed through her throbbing cock, painting Delia’s walls with cum and surging through her to flood her body with warmth. Delia’s old pussy was only barely able to keep the first few shots of cum inside, and by the time Jessie’s cock hit its second surge she was already overflowing. Cum oozed from the sides of Jessie’s cock against the seam of Delia’s pussy, and the steady dripping of the villain’s cream to Ash’s face fully began. Slowly, bit by bit...over his dozing features, his closed eyes, his lips, his hair...and that warm rain only continued when Jessie’s cock hit another spasm of pleasure and flooded Delia’s cunt with yet another burst.

This time, knowing that her bitch was already properly bred, Jessie yanked her cock from Delia’s pussy and instantly shoved it into her ass; switching holes with deft precision. She did it so quickly and with such force that she was able to unload yet another torrent into Delia’s tighter hole, and the older woman continued to tremble and twitch from the pleasure. While her ass was flooded with Jessie’s cum her pussy was left exposed and dripping, and with nothing to stop the tide a heavy batch of it squarely fell from her well-fucked hole and splashed unceremoniously on Ash’s face. It filled the room with a loud, wet noise that was completely unmistakeable to them both, and as Delia’s eyes went wide and fearful Jessie’s merely flashed with dominant glee that went well past sadistic.

“...mphf...what...the…”

Ash’s voice was soft as he started to stir, sounding almost like the boy he once was when he was under Delia’s care. In that moment of confusion as he started to stir, and while her cock was still spasming within Delia’s ass, Jessie merely beamed and claimed her victory. She shoved her gloved hands hard against the back of the older woman’s rump and forced her suddenly down; making her grind her cum-filled pussy against Ash’s face and making her go all the harder by thrusting fully into her ass. Delia shrieked a scream that had been building inside of her since this madness had begun, her eyes snapping open wide and her voice filling the bedroom with a sharp, piercing noise.

Still, she was utterly unable to pull away. She couldn’t pull away as Ash fumbled underneath her, clutching at her thighs and trying to break away, all the while inadvertently slurping and sucking on the pussy pressed to his face and leaking cum all over him. She couldn’t pull away as Jessie forced her to cunt-smother her son for a few long seconds, making him draw in long breaths laced with the scent of an old hole well-fucked by wicked dick. In fact, Jessie rolled her hips from side to side to make Delia grind across him, cackling all the way until she finally let them up. She pulled her prick free from Delia’s ass and allowed her to lift up off of Ash’s face, only to see that ribbons of her sticky white cum were still connecting the older woman’s folds to her son’s cheeks, lips, and hair. He was still in a state of outright shock at what was happening, but it started to come together when he looked past cum-blocked vision to see Jessie standing triumphantly over him.

“Y...You!” He coughed, wiped a hand over his face, and tried to get rid of the taste of her cum. “This...this is just like what you did to Misty! Who was it this time?! The girl I had a crush on before I le-”

Jessie answered Ash simply by yanking at Delia’s ponytail once more and dragging her to her feet. The shamed MILF, curvy and disgraced and bred by Ash’s greatest enemy, stood at Jessie’s side with tears on her face, a blush on her cheeks, and a frankly ludicrously amount of cum pouring from her pussy. As Ash’s eyes went even wider and he pushed back against the bed in revelation, Jessie merely chuckled and slapped a hand to her shaft, waving it gently back and forth. Delia knew what that meant, and she didn’t hesitate - without sparing her son a second glance she dropped to her knees, brought her cock to her lips, and started to clean up the mess. Just like Jessie had made Ash do for her.

“Well, twerp, I suppose this changes a few things between us.” Jessie beamed as she dropped a hand on Delia’s head, guiding her cock down the woman’s throat once more. “For starters...I think it’s time you start calling me Daddy!”

The End.

**Author's Note:**

> Hope you liked this rough and nasty story! 
> 
>  
> 
> [Check me on tumblr!](http://dracedomino.tumblr.com)


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